US11753430B2 - Method of making cobalt compounds for feed supplements - Google Patents
Method of making cobalt compounds for feed supplements Download PDFInfo
- Publication number
- US11753430B2 US11753430B2 US17/307,095 US202117307095A US11753430B2 US 11753430 B2 US11753430 B2 US 11753430B2 US 202117307095 A US202117307095 A US 202117307095A US 11753430 B2 US11753430 B2 US 11753430B2
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- US
- United States
- Prior art keywords
- mixture
- acid
- making
- cobalt compound
- set forth
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- 150000001869 cobalt compounds Chemical class 0.000 title claims abstract description 35
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 25
- 239000006052 feed supplement Substances 0.000 title claims abstract description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 84
- 239000000203 mixture Substances 0.000 claims abstract description 66
- 239000002253 acid Substances 0.000 claims abstract description 32
- 239000013078 crystal Substances 0.000 claims abstract description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- ZBYYWKJVSFHYJL-UHFFFAOYSA-L cobalt(2+);diacetate;tetrahydrate Chemical compound O.O.O.O.[Co+2].CC([O-])=O.CC([O-])=O ZBYYWKJVSFHYJL-UHFFFAOYSA-L 0.000 claims abstract description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 18
- 229910017052 cobalt Inorganic materials 0.000 claims description 11
- 239000010941 cobalt Substances 0.000 claims description 11
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 11
- 235000019260 propionic acid Nutrition 0.000 claims description 9
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 9
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 claims description 8
- NNNRGWOWXNCGCV-UHFFFAOYSA-N 4-(2-bromoethyl)benzonitrile Chemical class BrCCC1=CC=C(C#N)C=C1 NNNRGWOWXNCGCV-UHFFFAOYSA-N 0.000 claims description 6
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 6
- 239000000174 gluconic acid Substances 0.000 claims description 6
- 235000012208 gluconic acid Nutrition 0.000 claims description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 3
- 230000008020 evaporation Effects 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 239000004310 lactic acid Substances 0.000 claims description 3
- 235000014655 lactic acid Nutrition 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 239000010409 thin film Substances 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 159000000021 acetate salts Chemical class 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 229940011182 cobalt acetate Drugs 0.000 claims description 2
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 claims description 2
- 229910010272 inorganic material Inorganic materials 0.000 claims description 2
- 239000011147 inorganic material Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 description 8
- 229940049699 cobalt gluconate Drugs 0.000 description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- FDJOLVPMNUYSCM-WZHZPDAFSA-L cobalt(3+);[(2r,3s,4r,5s)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2r)-1-[3-[(1r,2r,3r,4z,7s,9z,12s,13s,14z,17s,18s,19r)-2,13,18-tris(2-amino-2-oxoethyl)-7,12,17-tris(3-amino-3-oxopropyl)-3,5,8,8,13,15,18,19-octamethyl-2 Chemical compound [Co+3].N#[C-].N([C@@H]([C@]1(C)[N-]\C([C@H]([C@@]1(CC(N)=O)C)CCC(N)=O)=C(\C)/C1=N/C([C@H]([C@@]1(CC(N)=O)C)CCC(N)=O)=C\C1=N\C([C@H](C1(C)C)CCC(N)=O)=C/1C)[C@@H]2CC(N)=O)=C\1[C@]2(C)CCC(=O)NC[C@@H](C)OP([O-])(=O)O[C@H]1[C@@H](O)[C@@H](N2C3=CC(C)=C(C)C=C3N=C2)O[C@@H]1CO FDJOLVPMNUYSCM-WZHZPDAFSA-L 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- 210000004767 rumen Anatomy 0.000 description 3
- 238000000527 sonication Methods 0.000 description 3
- 239000011715 vitamin B12 Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- VPUKOWSPRKCWBV-UHFFFAOYSA-L cobalt(2+);2-hydroxypropanoate Chemical compound [Co+2].CC(O)C([O-])=O.CC(O)C([O-])=O VPUKOWSPRKCWBV-UHFFFAOYSA-L 0.000 description 2
- TZWGXFOSKIHUPW-UHFFFAOYSA-L cobalt(2+);propanoate Chemical compound [Co+2].CCC([O-])=O.CCC([O-])=O TZWGXFOSKIHUPW-UHFFFAOYSA-L 0.000 description 2
- ASKVAEGIVYSGNY-UHFFFAOYSA-L cobalt(ii) hydroxide Chemical compound [OH-].[OH-].[Co+2] ASKVAEGIVYSGNY-UHFFFAOYSA-L 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 235000010350 erythorbic acid Nutrition 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 229910021503 Cobalt(II) hydroxide Inorganic materials 0.000 description 1
- CIWBSHSKHKDKBQ-DUZGATOHSA-N D-araboascorbic acid Natural products OC[C@@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-DUZGATOHSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000282849 Ruminantia Species 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- -1 butyric Chemical class 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 229910021446 cobalt carbonate Inorganic materials 0.000 description 1
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
- 229910000428 cobalt oxide Inorganic materials 0.000 description 1
- ZOTKGJBKKKVBJZ-UHFFFAOYSA-L cobalt(2+);carbonate Chemical compound [Co+2].[O-]C([O-])=O ZOTKGJBKKKVBJZ-UHFFFAOYSA-L 0.000 description 1
- IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical compound [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000004318 erythorbic acid Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 229940026239 isoascorbic acid Drugs 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N linoleic acid group Chemical group C(CCCCCCC\C=C/C\C=C/CCCCC)(=O)O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 125000005481 linolenic acid group Chemical group 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/06—Cobalt compounds
- C07F15/065—Cobalt compounds without a metal-carbon linkage
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D1/00—Evaporating
- B01D1/06—Evaporators with vertical tubes
- B01D1/065—Evaporators with vertical tubes by film evaporating
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/105—Aliphatic or alicyclic compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K50/00—Feeding-stuffs specially adapted for particular animals
- A23K50/10—Feeding-stuffs specially adapted for particular animals for ruminants
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D1/00—Evaporating
- B01D1/22—Evaporating by bringing a thin layer of the liquid into contact with a heated surface
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D9/00—Crystallisation
- B01D9/0004—Crystallisation cooling by heat exchange
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D9/00—Crystallisation
- B01D9/004—Fractional crystallisation; Fractionating or rectifying columns
- B01D9/0045—Washing of crystals, e.g. in wash columns
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D9/00—Crystallisation
- B01D9/0081—Use of vibrations, e.g. ultrasound
Definitions
- the present invention relates to feed supplements, and more particularly to a method of making cobalt compounds for feed supplements.
- Cobalt is a component of Vitamin B 12 .
- Vitamin B 12 is produced in ruminant animals by microorganisms in the rumen.
- Cobalt can be provided in feed supplements for livestock, such as cattle, goats and sheep, to prevent Vitamin B 12 deficiency.
- cobalt compounds cannot be used in feed supplements. Some cobalt compounds, such as cobalt metal and dicobalt carbonyl are toxic. Cobalt carbonate has been used as a feed supplement for many years, but a significant portion of it is not taken up easily by many of the microorganisms in the rumen. Cobalt chloride releases hydrogen chloride which can deactivate enzymes and is an irritant on the tongue. Cobalt oxide and cobalt hydroxide are very insoluble at physiological temperatures and are not useful in feed supplements.
- Cobalt lactate, cobalt propionate, cobalt gluconate and cobalt heptogluconate can be used in feed supplements.
- the bioavailability of these compounds can be improved by increasing the relative surface area.
- Prior known methods for producing these compounds have required high temperatures, high magnetic fields or grinding the product of the chemical reaction.
- a method of making a cobalt compound for feed supplements includes the steps of dissolving cobalt acetate tetrahydrate in water at a selected temperature to form a mixture, adding a selected acid to the mixture, sonicating the mixture for a selected time, removing acetic acid from the mixture, and separating crystals of the cobalt compound from the mixture.
- the method may include the step of stirring or rotating the mixture during the step of sonicating.
- the step of separating may also include the substep of precipitating the crystals from the mixture by cooling the mixture.
- a method of making a cobalt compound for feed supplements includes the steps of dissolving cobalt acetate tetrahydrate in water at a selected temperature to form a mixture, adding a selected acid to the mixture, sonicating the mixture for a selected time, removing acetic acid from the mixture, and separating crystals of the cobalt compound from the mixture.
- the selected acid can be any carboxylic acid.
- lactic, propionic, gluconic and heptogloconic are used to produce cobalt lactate, cobalt propionate, cobalt gluconate and cobalt heptogluconate, respectively.
- the cobalt acetate tetrahydrate is dissolved in a minimum of water at between 55° C. and 70° C.
- the subsequent steps are modified depending on the pKa and boiling point of the selected acid.
- Acetic acid has a pKa of 4.75.
- the step of adding includes dissolving the selected acid in a minimum of water at 55° C. and adding the selected acid so that the mole ratio of acid to cobalt is preferably 2.02 or more, more preferably 2.13 or more and most preferably 2.25 or more.
- the method may include the step of stirring the mixture during the step of sonicating.
- the step of sonicating includes sonicating the mixture at about 0.25 watts/cm 2 at 20-55 KHz, or sufficient power that standing waves are clearly visible, for about one hour.
- the step of separating includes the substep of reducing the temperature to 17° C. or below, during the step of sonicating, to precipitate the crystals from the mixture.
- the step of separating can also include the substeps of filtering, washing with cold water to remove acetic acid and drying the crystals.
- the step of removing acetic acid from the mixture can include sparging with a wet stream of nitrogen at 55° C. or subjecting the mixture to thin film evaporation of acetic acid under reduced pressure or both.
- the step of adding includes adding the selected acid so that the mole ratio of acid to cobalt is 2.25 or more.
- the method can include the step of rapidly rotating the mixture during the step of sonicating.
- the step of sonicating includes sonicating the mixture at 55° C. at about 0.3 watts/cm 2 at 20-55 KHz.
- the step of removing acetic acid from the mixture can include subjecting the mixture to thin film evaporation of acetic acid under reduced pressure.
- the step of adding includes adding the propionic acid so that the mole ratio of acid to cobalt is 3.0 or more.
- the method includes the step of rapidly rotating the mixture during the step of sonicating.
- the step of sonicating includes sonicating the mixture at 55° C. and at about 0.4 watts/cm 2 at 20-55 KHz.
- the step of removing acetic acid from the mixture includes slowly evacuating acetic acid at reduced pressure while adding 95% propionic acid as needed.
- the azeotrope of water and propionic acid boils at about 99° C. and acetic acid boils at about 117° C., at atmospheric pressure.
- Propionic acid boils at about 42° C. at 20 mm Hg, and acetic acid boils at about 17° C. at 10 mm Hg.
- the step of separating can also include vacuum drying the mixture. The temperature is kept below about 70° C. to prevent formation of sticky cobalt hydroxides.
- the step of removing acetic acid can include blending the mixture into basic inorganic materials that then form acetate salts, primarily with calcium, magnesium, potassium or sodium ions.
- the step of separating can include containing the crystals in a slurry, suspension, or gel.
- the method can also include a step of forming a premix, including the substeps of adding, after the step of dissolving, gluconic acid to provide an almost 1:1 premix mixture of cobalt acetate and cobalt gluconate compounds, and then sonicating the premix mixture.
- the premix remained in solution at 15° C. for over ten days.
- additional gluconic acid 1.1 eq of total gluconic acid to acetic acid
- Sonicating the mixture with ultrasonic frequencies causes pressure waves where molecules are jostled apart, promoting both the exchange of acetic acid to the selected acid and promoting formation of fine crystals.
- the method produces cobalt compounds for feed supplements without requiring high temperatures, high magnetic fields or grinding the product of the chemical reaction.
- the method produces fine crystals with a relatively high surface area and high bioavailability for the microorganisms in the rumen.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Food Science & Technology (AREA)
- Physics & Mathematics (AREA)
- Thermal Sciences (AREA)
- Birds (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (20)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US17/307,095 US11753430B2 (en) | 2020-06-03 | 2021-05-04 | Method of making cobalt compounds for feed supplements |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US202063034162P | 2020-06-03 | 2020-06-03 | |
US17/307,095 US11753430B2 (en) | 2020-06-03 | 2021-05-04 | Method of making cobalt compounds for feed supplements |
Publications (2)
Publication Number | Publication Date |
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US20210380621A1 US20210380621A1 (en) | 2021-12-09 |
US11753430B2 true US11753430B2 (en) | 2023-09-12 |
Family
ID=78818461
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US17/307,095 Active US11753430B2 (en) | 2020-06-03 | 2021-05-04 | Method of making cobalt compounds for feed supplements |
Country Status (1)
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US (1) | US11753430B2 (en) |
Citations (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3133942A (en) | 1960-12-03 | 1964-05-19 | Basf Ag | Production of metal salts of organic acids |
US3198635A (en) | 1964-04-17 | 1965-08-03 | Feed Service Corp | Nutrient compositions and process for preparing same |
US4009263A (en) | 1974-02-15 | 1977-02-22 | Shafer Laverne | Energized cobalt-containing animal feed |
US4060535A (en) | 1976-08-31 | 1977-11-29 | Tenneco Chemicals, Inc. | Process for the production of metal salts of organic acids |
USRE32909E (en) | 1980-10-07 | 1989-04-18 | Biosystems Research Inc. | Metal oxycarboxylates and method of making same |
US5591878A (en) | 1995-09-19 | 1997-01-07 | Kemin Industries, Inc. | Catalyzed process for producing metal carboxylates for use as animal feed supplements |
US5622739A (en) | 1995-06-06 | 1997-04-22 | K.E.S. Associates | Feed block with improved mineral delivery |
US5707679A (en) | 1994-09-30 | 1998-01-13 | Kemin Industries, Inc. | Metal propionates for use as animal feed supplements |
US5795615A (en) | 1994-09-30 | 1998-08-18 | Kemin Industries, Inc. | Process for producing metal carboxylates for use as animal feed supplements |
US7495117B2 (en) | 2006-08-04 | 2009-02-24 | Kemin Industries, Inc. | Metal carboxylate salts |
US8182573B2 (en) | 2005-09-06 | 2012-05-22 | ETH Zürich | Methods and devices for flame spray pyrolysis |
US8575212B2 (en) | 2009-12-22 | 2013-11-05 | Ralco Nutrition, Inc. | Organically chelated mineral compositions and methods thereof |
US9663438B2 (en) | 2015-09-04 | 2017-05-30 | Nutech Biosciences, Inc. | Process for forming chromium propionate as an agricultural feed additive |
US10265340B2 (en) | 2012-02-22 | 2019-04-23 | Kemin Industries, Inc. | Animal feed compositions and methods of using the same |
US20210015120A1 (en) * | 2019-07-16 | 2021-01-21 | Ralco Nutrition, Inc. | Feed compositions |
-
2021
- 2021-05-04 US US17/307,095 patent/US11753430B2/en active Active
Patent Citations (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3133942A (en) | 1960-12-03 | 1964-05-19 | Basf Ag | Production of metal salts of organic acids |
US3198635A (en) | 1964-04-17 | 1965-08-03 | Feed Service Corp | Nutrient compositions and process for preparing same |
US4009263A (en) | 1974-02-15 | 1977-02-22 | Shafer Laverne | Energized cobalt-containing animal feed |
US4060535A (en) | 1976-08-31 | 1977-11-29 | Tenneco Chemicals, Inc. | Process for the production of metal salts of organic acids |
USRE32909E (en) | 1980-10-07 | 1989-04-18 | Biosystems Research Inc. | Metal oxycarboxylates and method of making same |
US5707679A (en) | 1994-09-30 | 1998-01-13 | Kemin Industries, Inc. | Metal propionates for use as animal feed supplements |
US5795615A (en) | 1994-09-30 | 1998-08-18 | Kemin Industries, Inc. | Process for producing metal carboxylates for use as animal feed supplements |
US5622739A (en) | 1995-06-06 | 1997-04-22 | K.E.S. Associates | Feed block with improved mineral delivery |
US5591878A (en) | 1995-09-19 | 1997-01-07 | Kemin Industries, Inc. | Catalyzed process for producing metal carboxylates for use as animal feed supplements |
US8182573B2 (en) | 2005-09-06 | 2012-05-22 | ETH Zürich | Methods and devices for flame spray pyrolysis |
US7495117B2 (en) | 2006-08-04 | 2009-02-24 | Kemin Industries, Inc. | Metal carboxylate salts |
US8575212B2 (en) | 2009-12-22 | 2013-11-05 | Ralco Nutrition, Inc. | Organically chelated mineral compositions and methods thereof |
US10265340B2 (en) | 2012-02-22 | 2019-04-23 | Kemin Industries, Inc. | Animal feed compositions and methods of using the same |
US9663438B2 (en) | 2015-09-04 | 2017-05-30 | Nutech Biosciences, Inc. | Process for forming chromium propionate as an agricultural feed additive |
US20210015120A1 (en) * | 2019-07-16 | 2021-01-21 | Ralco Nutrition, Inc. | Feed compositions |
Also Published As
Publication number | Publication date |
---|---|
US20210380621A1 (en) | 2021-12-09 |
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